Iodonitrene-Mediated Nitrogen Transfer to Alkenes for the Direct Synthesis of NH-Aziridines.

This work presents a novel and efficient method for the direct synthesis of NH-aziridines from a broad range of alkenes under mild conditions. The developed method uses aqueous ammonia and (diacetoxyiodo)benzene (PIDA) at 0 °C, offering a straightforward and atom-economical approach. Notably, this approach addresses the common challenge of chemoselectivity, effectively preventing the overoxidation of aziridines to nitriles. Mechanistic studies support the involvement of an in situ-generated iodonitrene as the key nitrogen-transfer intermediate. Overall, this method represents a significant advancement in aziridine synthesis, combining simplicity and selectivity, and complements the existing procedures for the direct NH insertion into alkenes.